7/2/2007: Stephen Has Completed "When I Was Your Age"

Here are the costs of some things in 1940:

Car: $800
Gasoline: 18 cents/gal
House: $6,550
Bread: 8 cents/loaf
Milk: 34 cents/gal
Postage Stamp: 3 cents
Stock Market: 131
Average Annual Salary: $1,900
Minimum Wage: 30 cents per hour
(Source)

That covers all the requirements except clothes.
Using interpolation from the other items, I estimate a shirt, pants, socks, and shoes would cost between $3 and $4.